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Aromatic diamine compound and aromatic dinitro compound

a technology of aromatic diamine and dinitro compound, which is applied in the preparation of amino compounds, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of aromatic diamine having an oligomer structure, reducing heat resistance, and poor solvent workability, etc., and achieves low water absorption, excellent heat resistance, and low dielectric characteristics.

Inactive Publication Date: 2012-12-27
UERA KAZUYOSHI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides a novel aromatic diamine compound and a novel aromatic dinitro compound that can be used to obtain high molecular weight materials with low heat resistance, low dielectric constant, low dielectric loss tangent, and low water absorption coefficient. These compounds have excellent properties that make them useful in a variety of applications. The invention also provides a process for the production of these compounds using a specific bifunctional phenylene ether oligomer and a monofunctional phenol compound."

Problems solved by technology

However, the aromatic diamines having fluorine atoms have a problem about a decrease in heat resistance.
However, a problem is that workability such as solubility in solvent is poor (for example, JP-A-10-152559).
However, such aromatic diamine having an oligomer structure has not been found yet.

Method used

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  • Aromatic diamine compound and aromatic dinitro compound
  • Aromatic diamine compound and aromatic dinitro compound
  • Aromatic diamine compound and aromatic dinitro compound

Examples

Experimental program
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Effect test

synthetic example 1

(Synthesis of Bifunctional Phenylene Ether Oligomer)

[0057]A longitudinally long reactor having a volume of 12 liters and equipped with a stirrer, a thermometer, an air-introducing tube and baffleplates was charged with 3.88 g (17.4 mmol) of CuBr2, 0.75 g (4.4 mmol) of N,N′-di-t-butylethylenediamine, 28.04 g (277.6 mmol) of n-butyldimethylamine and 2,600 g of toluene. The mixture was stirred at a reaction temperature of 40° C. Separately, 129.32 g (0.48 mol) of 2,2′,3,3′,5,5′-hexamethyl-(1,1′-biphenyl)-4,4′-diol, 292.19 g (2.40 mol) of 2,6-dimethylphenol, 0.51 g (2.9 mmol) of N,N′-di-t-butylethylenediamine and 10.90 g (108.0 mmol) of n-butyldimethylamine were dissolved in 2,300 g of methanol, to obtain a mixed solution. The mixed solution was dropwise added to the mixture in the reactor over 230 minutes with stirring. During the above addition of the mixed solution, bubbling was continuously carried out with a nitrogen-air mixed gas having an oxygen concentration of 8% at a flow velo...

synthetic example 2

(Synthesis of Bifunctional Phenylene Ether Oligomer)

[0058]A longitudinally long reactor having a volume of 12 liters and equipped with a stirrer, a thermometer, an air-introducing tube and baffleplates was charged with 9.36 g (42.1 mmol) of CuBr2, 1.81 g (10.5 mmol) of N,N′-di-t-butylethylenediamine, 67.77 g (671.0 mmol) of n-butyldimethylamine and 2,600 g of toluene. The mixture was stirred at a reaction temperature of 40° C. Separately, 129.32 g (0.48 mol) of 2,2′,3,3′,5,5′-hexamethyl-(1,1′-biphenyl)-4,4′-diol, 878.4 g (7.2 mol) of 2,6-dimethylphenol, 1.22 g (7.2 mmol) of N,N′-di-t-butylethylenediamine and 26.35 g (260.9 mmol) of n-butyldimethylamine were dissolved in 2,300 g of methanol, to obtain a mixed solution. The mixed solution was dropwise added to the mixture in the reactor over 230 minutes with stirring. During the above addition of the mixed solution, bubbling was continuously carried out with a nitrogen-air mixed gas having an oxygen concentration of 8% at a flow veloc...

synthetic example 3

(Synthesis of Bifunctional Phenylene Ether Oligomer)

[0059]A longitudinally long reactor having a volume of 12 liters and equipped with a stirrer, a thermometer, an air-introducing tube and baffleplates was charged with 13.1 g (0.12 mol) of CuCl, 707.0 g (5.5 mol) of di-n-butylamine and 4,000 g of methyl ethyl ketone. The mixture was stirred at a reaction temperature of 40° C. A solution of 410.2 g (1.6 mol) of 4,4′-methylenebis(2,6-dimethylphenol) and 586.5 g (4.8 mol) of 2,6-dimethylphenol in 8,000 g of methyl ethyl ketone was dropwise added to the mixture in the reactor over 120 minutes with stirring. During the above addition of the solution, bubbling was continuously carried out with 2 L / min of air. A disodium dihydrogen ethylenediamine tetraacetate aqueous solution was added the stirred mixture to terminate the reaction. Then, washing was three times carried out with 1N hydrochloric acid aqueous solution and then washing was carried out with ion-exchanged water. The thus-obtain...

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Abstract

A novel aromatic diamine compound obtained by introducing aromatic amino groups into both terminals of a specific bifunctional phenylene ether oligomer and a novel aromatic dinitro compound obtained by introducing aromatic nitro groups into both terminals of a specific bifunctional phenylene ether oligomer, these compounds being used as raw materials for obtaining high molecular weight materials having high heat resistance, a low dielectric constant, a low dielectric loss tangent and a low water absorption coefficient.

Description

FIELD OF THE INVENTION[0001]The present invention relates to a novel aromatic diamine compound and a novel aromatic dinitro compound, each of which is obtained from a bifunctional phenylene ether oligomer having a specific structure as a raw material.BACKGROUND OF THE INVENTION[0002]Conventionally, aromatic diamine compounds are widely used as raw materials for functional high molecular weight materials such as bismaleimide, polyimide and thermosetting epoxy resins. In recent years, higher performance has been required in these fields so that higher physical properties have been more and more required as functional high molecular weight materials. As such physical properties, for example, heat resistance, weather resistance, chemical resistance, low water absorption properties, high fracture toughness, low dielectric constant, low dielectric loss tangent, moldability, flexibility, dispersibility in solvent and adhesive properties are required.[0003]In the fields of information commu...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G65/48C08G65/40
CPCC07C217/90C07C205/38C07C209/32
Inventor UERA, KAZUYOSHIOHNO, DAISUKEISHII, KENJJI
Owner UERA KAZUYOSHI
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